Robert Sean Derby

**looking to relocate to Seattle, Washington

Director of Technology with over 20 years of experience leading technology departments to align with and promote organizational strategic goals. Highly experienced with the specific needs, planning, and culture of nonprofit organizations. Comprehensive experience managing diverse technology environments, including infrastructure planning, vendor partnerships, security, disaster planning and business continuity, modern hybrid work environments, digital asset management, website design, analytics, and customer relationship building. Recognized for strong leadership abilities and collaboration skills, adept at guiding cross-functional teams and advancing initiatives that boost organizational innovation, transformation, and efficiency.

What I Do

Microsoft 356

Expertise with Microsoft environments, including Microsoft 365 design and administration, SharePoint, Teams, Office, and the new Microsoft Viva suite.

Digital Transformation & Innovation

Experience leading digital initiatives, including developing OTT platforms for FVOD/SVOD/TVOD environments and livestream production. YouTube management and channel growth. Website planning and design.

Data Analytics & Business Intelligence

Experience developing Power Platform solutions including comprehensive Power BI reports, Model-Driven and Canvas Power Apps, and Power Automation workflows.

Strategic Leadership

Highly experienced with aligning organizational goals with technology strategy. Expertise leading cross organizational teams focused on technology planning.

Resume

Experience

2020 - Current
The Dallas Opera

Director of IT

  • Spearheaded the digital transformation of The Dallas Opera, modernizing infrastructure and applications to enhance performance, reliability, and user engagement. This includes moving the infrastructure to an Azure cloud environment, upgrading security and PCI compliance, budgeting and deploying new equipment, developing a modern workplace Microsoft 365 structure to support hybrid work, and updating the technology support structure.
  • Led the design and implementation the Opera’s first digital TVOD/FVOD (OTT) platform, upgraded YouTube channel to the partner program, and deployed a modern digital website; significantly expanding the organization's reach and creating new revenue streams through digital content.
  • Founding member and lead of the "Digital Innovation Team," a cross-organizational group of experts and decision-makers, guiding The Dallas Opera's digital initiatives to further our mission. This initiative fostered a culture of innovation, significantly enhancing our digital outreach and engagement.
  • Balance organizational growth and technology evolution with strong security fundamentals, including upgrading security systems, vendor relationships, PCI compliance, employee security awareness, and disaster planning.
  • Highly skilled with Microsoft 365 environments, including Office, Teams, SharePoint, and the new Microsoft Viva employee experience and engagement suite.
  • Microsoft Power Platform development, including advanced Power BI analytics dashboards for the organization pulling data from multiple databases via API. Creating Power Apps for opera production management and planning.
  • Researching next-gen tech solutions, positioning the organization to understand and prepare for upcoming changes. Currently looking at AI potential for nonprofits.
2003 - 2020
La Jolla Country Day School

Director of Technology

  • Director of Technology for a N-12 Independent school, overseeing a complex campus environment of 600+ mixed Mac/PC devices and an additional 700+ BYOD student devices. Oversaw years of campus technology infrastructure development, including multiple new buildings, complex indoor/outdoor Wi-Fi, security, and application growth. Provided comprehensive technology leadership, team support and training for over 200 faculty and staff, alongside support for 800+ students and visitors for events.
  • Led a team of 4-6 technology professionals and additional contractors, taking full responsibility for hiring, evaluations, and professional development. Set department goals and steered the direction to align with organizational objectives, demonstrating strong leadership and strategic planning skills.
  • Functioned as the principal architect for technology planning and implementation, playing a pivotal role in advancing the organization’s strategic goals. Embraced a forward-thinking approach to leadership, fostering a culture of innovation and collaboration across all sectors of the school community.
  • Managed an annual technology budget ranging from $700,000 to $1,000,000, meticulously overseeing all technology-related purchases. Worked in close coordination with the CFO to align technology investments with the organization’s financial strategies and goals.
  • Administered a wide array of systems including Active Directory, Office 365, Google Apps, Student Information Systems (Blackbaud), Learning Management Systems (Blackbaud and Blackboard), ensuring robust and efficient operational support. Played a key role in providing backup and support for staff managing various critical systems.
  • Innovated in the field of educational analytics by designing Power Platform solutions that revolutionized the organization's approach to data analysis within academics.
  • Served as a futurist, guiding the organization through the exploration and adoption of emerging technologies. Engaged actively with students and faculty to discuss and implement trending technologies, significantly impacting education and societal norms.
2002 -2003
VUNETUSA Technologies

Systems Administrator

  • Recruited to VUNETUSA Technologies following its acquisition of the RollingStone.com organization, reflecting their wish for my experience in managing complex digital platforms. Entrusted with the administration and support of a diverse and expansive technology network of 1000+ Linux/Solaris/Windows systems across various high-profile digital properties including MP3.com, Pressplay.com, Emusic.com, Moviso.com, and Rollingstone.com.
  • Oversaw the seamless configuration, maintenance, and repair of critical systems, ensuring robust operational efficiency and reliability. Participated in an on-call rotation for off-hours systems support to maintain continuous network performance.
  • Played a key role in DNS and F5 BigIP work queues management, executing daily adjustments to zone files and BigIP configurations. These actions were crucial for the addition or modification of system clusters, enhancing the scalability and responsiveness of our digital infrastructure.
  • Directly managed the infrastructure for Rollingstone.com (Windows 2000, IIS, SQL 7.0), from the initial system builds to ongoing modifications and troubleshooting. My stewardship ensured the platform's high availability and optimal performance.
  • Functioned as the primary administrator for EMC disk tower systems, orchestrating coordination with the EMC vendor for routine preventative maintenance, urgent repairs, and strategic long-term upgrade projects. This responsibility underscored my capacity to manage critical data storage solutions effectively.
  • Demonstrated exceptional communication skills by coordinating all department maintenance announcements to various stakeholders, ensuring transparency and alignment across the organization.
  • Significantly contributed to the team responsible for the growth and digital innovations of MP3.com, a pioneer in online music distribution, by managing and optimizing the underlying technology infrastructure. This role involved adapting to rapid technological advancements and user growth, positioning the platform at the forefront of the digital music revolution.
1999 -2002
RollingStone.com

Managing Infrastructure Engineer

  • Led the technology infrastructure management for RollingStone.com, the digital presence of the iconic magazine, planning and overseeing an array of 20+ Windows 2000/IIS 5.0 production web servers, Windows 2000/SQL Server 2000 database servers, and multiple application servers. Oversaw the infrastructure deployed across two Exodus Communication co-location centers and enhanced with F5 3DSN/BigIP equipment for optimal performance and reliability.
  • Led a team dedicated to maintaining the infrastructure essential for supporting RollingStone.com’s venture into the digital media landscape of the early 2000s. Worked to ensure the continuous delivery of dynamic content and services, crucial for engaging the brand's global online audience.
  • Orchestrated the acquisition, setup, and maintenance of all necessary hardware/software, establishing a solid foundation for the website's operations. Instituted comprehensive monitoring and support mechanisms for the website and associated systems, maintaining high availability and content fidelity through systematic code/content replication and detailed traffic analysis.
  • Managed a broad range of IT responsibilities for the office network, including more than 20 Windows 2000/NT servers, MS Exchange, SMS, firewalls, RAS setup, and providing desktop support for over 120 users. This framework supported the company's internal operations and communication needs.
  • As a leader in the company's IT strategy, influenced key decisions regarding hardware/software selection, vendor management, and IT budgeting, displaying a comprehensive approach to technological resource management.
  • Successfully led several critical IT projects that significantly enhanced RollingStone.com’s infrastructure, including a major data center co-location transition and a system-wide upgrade from Windows NT 4.0 to Windows 2000. The ultimate project involved a comprehensive overhaul of the IT infrastructure for the VUNetUSA network, featuring automated OS installations, Active Directory configurations, SQL server setups, and bespoke configurations for various websites.
  • A central member of the leadership team helping steer RollingStone.com through the digital media evolution, spearheading innovations that established the site as a leader in digital publishing during the early 2000s.

Education

2001

MCP (Microsoft Certified Professional) Windows 2000

  • Installing, Configuring, and Administering Microsoft Windows 2000 Professional
  • Installing, Configuring, and Administering Microsoft Windows 2000 Server
  • Installing and Administering a Microsoft Windows 2000 Network Infrastructure
2001

CCNA (Cisco Certified Network Associate)

1998

MCSE (Microsoft Certified System Engineer) NT 4.0

  • Networking Essentials
  • Implementing and Supporting MS Windows NT Server 4
  • Implementing and Supporting MS Windows NT Server 4 – Enterprise
  • Implementing and Supporting MS Windows NT Workstation 4
  • Internetworking with Microsoft TCP/IP on MS Windows NT 4
  • Implementing and Supporting MS Exchange Server 5.5
1993
University of Michigan

B.A., Psychology 1993

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